Field of the Invention
The present application relates to novel pyridyloxyalkylcarboxamides and to their use as endoparasiticides against endoparasites in animals or humans, and to their use as nematicides for controlling phytopathogenic nematodes, and furthermore to endoparasiticides and nematicides comprising pyridyloxyalkylcarboxamides.
Description of Related Art
In the field of veterinary medicine, the occurrence of resistances against all commercially available anthelmintics is an increasing problem which requires endoparasiticides having novel molecular mechanisms of action. Such compounds should exhibit excellent efficacy against a broad spectrum of helminths and nematodes and at the same time not cause any toxic effects in the animals treated.
In the field of crop protection, too, nematodes may cause considerable yield losses, and they are therefore also controlled with active chemical compounds having nematicidal activity. To this end, suitable active compounds should have high activity and a broad spectrum of action against various species of nematodes, and at the same time be toxicologically safe for non-target organisms.
WO-A 2001/060783 claims certain phenacylbenzamides for oral use as anthelmintics in veterinary medicine.
Isothiazolecarboxamides are known from WO-A 1999/24413, heterocyclylethylcarboxamide derivatives from WO-A 2006/108791, heterocyclylethylbenzamide derivatives from WO-A 2006/108792, N-(1-methyl-2-phenylethyl)benzamides from WO-A 2007/060162, N-(1-methyl-2-phenylethyl)carboxamides from WO-A 2007/060164, N-phenethylcarboxamide derivatives from WO-A 2007/060166, N-(3-phenylpropyl)carboxamides from WO-A 2008/101976, pyrazolecarboxamides from WO-A 2008/148570 and WO-A 2010/063700, pyrazinylcarboxamides from WO-A 2011/128989, various 2-pyridylethylcarboxamide derivatives from WO-A 2004/016088, WO-A 2004/074280, WO-A 2005/014545, WO-A 2005/058828, WO-A 2005/058833 and WO-A 2005/085238 and pyridyloxyalkylcarboxamides from WO-A 2009/012998 as agrochemical fungicides. WO-A 2011/151370 describes N-[(het)arylalkyl)]pyrazolecarboxamides or -thiocarboxamides as fungicides. Furthermore, WO-A 2007/108483/EP-A 1 997800 describes N-2-(hetero)arylethylcarboxamide derivatives as fungicides and nematicides. WO-A 2008/126922 explicitly claims the use of 2-pyridylethylcarboxamide derivatives for use against nematodes in crop cultivation. WO-A 2012/118139 also embraces phenyl(oxy)ethylcarboxamides and 2-pyridyl(oxy)ethylcarboxamides as endoparasiticides; however, these are only embodied as benzamides. DE 103 07 845 A1 discloses heterocyclic amides as pesticides, the compounds 1009 and 1011 being part of the class of compounds disclosed herein and therefore excluded from the scope of the invention.
Further nematicidal and/or anthelmintic patent applications were published after the priority date of the present application: WO-A 2013/064460 and WO-A 2013/064461 describe pyridylethylcarboxamides and their use as nematicides. WO-A 2013/076230 also claims phenyloxyethylcarboxamides and their use as medicaments for controlling endoparasites in animals or humans.
The use of the pyridyloxyalkylcarboxamides of the prior art as endoparasiticides in the field of veterinary medicine and as nematicides in crop cultivation has hitherto not been described.
In the literature, there are indications that by incorporating oxygen in the vicinity of the heteroaromatic system it may be possible to overcome the disadvantages of the metabolic instability of a benzylic CH2 group. Accordingly, the present application describes novel pyridyloxyalkylcarboxamides and their use as endoparasiticides against endoparasites in animals or humans, and their use as nematicides for controlling phytopathogenic nematodes, and furthermore endoparasiticides and nematicides comprising pyridyloxyalkylcarboxamides.